当前位置: X-MOL 学术Biosci. Biotechol. Biochem. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Syntheses of all eight stereoisomers of conidendrin.
Bioscience, Biotechnology, and Biochemistry ( IF 1.6 ) Pub Date : 2020-06-17 , DOI: 10.1080/09168451.2020.1777081
Hinako Shirakata 1 , Hisashi Nishiwaki 1 , Satoshi Yamauchi 1
Affiliation  

All eight stereoisomers of conidendrin were synthesized from (1 R,2 S,3 S)-1-(4-benzyloxy-3-methoxyphenyl)-3-(4-benzyloxy-3-methoxybenzyl)-2- hydroxymethyl-1,4-butanediol ((+)-4) and its enantiomer with high optical purity. The configurations at 4-positions of the conidendrin stereoisomers were constructed by intramolecular Friedel-Crafts reaction of protected 4. After conversion to tetrahydronaphthalene intermediate 7a, the 2- and 3-position of tetrahydronaphthalene structure 7a were converted to 3a- and 9a-position of (+)-α-conidendrin (3a), respectively. By the epimerization process of 2- or 3-position of 7a, the other diastereomers were obtained. All enantiomers were also synthesized from (−)-4.



中文翻译:

孢子烯苷的所有八个立体异构体的合成。

从(1 R,2  S,3  S)-1-(4-苄氧基-3-甲氧基苯基)-3-(4-苄氧基-3-甲氧基苄基)-2-羟甲基-1,4合成分生孢子蛋白的所有八个立体异构体 -具有高光学纯度的-丁二醇((+)- 4)及其对映异构体。通过被保护的4的分子内Friedel-Crafts反应,构建了分生孢子蛋白立体异构体4位的构型。转化为四氢萘中间体7a后,将四氢萘结构7a的2-位和3-位分别转化为(+)-α-分枝烯苷(3a)的3a位和9a位。通过2a或3位7a的差向异构过程,获得了其他非对映异构体。所有对映体也由(-)- 4合成。

更新日期:2020-06-17
down
wechat
bug